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Holiday rentals in Kailua

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Top-rated holiday rentals in Kailua

Guests agree: these stays are highly rated for location, cleanliness and more.

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Home in Kailua

4.84 out of 5 average rating, 366 reviews

Kailua Beach Park - 1 BR Cottage

Kailua Beach was once again been rated as the best beach in the USA for 2019, by Dr. Beach." The cottage is directly across the street from Kailua Beach Park and less than a 2-minute walk to step into the ocean. It is a legal vacation rental, license number 1990/NUC-1758. The property is tucked away one house back from the road into Lanikai, and described by guests as "a little oasis of quiet and calm." The bathroom has been remodeled with a new showers, sinks and plumbing fixtures April 2022!

Guest favourite

Apartment in Kahuku

5 out of 5 average rating, 152 reviews

HawaiianaLuxe_Townhouse at Turtle Bay_Hale LuLu

Come to escape to this newly renovated 1,150SF 2 bedrooms/2.5 bathroom townhouse for a soul comforting Northshore stay! Away from hustling downtown, Hale Lulu sits peacefully a few minutes away from iconic Turtle Bay Hotel and the most beautiful secluded beaches and trails! This unit is the biggest model in Kulima West. We offer 2 king size beds and 1 queen bed in three different bedrooms for your restful stay. The best cleaning crew was hired for your luxurious staying experience in Hawaii.

Guest favourite

Apartment in Kahuku

4.93 out of 5 average rating, 176 reviews

SEArider TWO at Turtle Bay (1 bedroom / 1 bath)

Our number one priority at SEArider is to provide our guests with a luxury Hawaiian experience. This unit has been completely renovated with our main focus being quality and comfort. Nestled in the condominiums that surround Turtle Bay, TWO has a luxurious but minimal feel with a mauka (mountain) inspired theme. Key features include locally made and dyed linens and waffle print towels. TWO sits directly below our other property, SEArider ONE (please search us on Air BnB for photos and reviews.)

Guest favourite

Apartment in Waianae

4.97 out of 5 average rating, 239 reviews

Beachfront Getaway - Hawaiian Princess Condo

Mesmerizing sunset views from this sandy beach front condo. Nothing separates you from sparkling turquoise waters but footprints in the sand. Balcony is ideal height for turtle watching. From Nov- April you may spot a whale. This vibrant land is full of surprises. Even dolphins spin by now and then. Escape the crowds of Waikiki to experience a real Hawaiian lifestyle. Snorkel, boogie board or surf right out your door. Awakening to the rhythm of the ocean can change your life forever.

Guest favourite

Home in Hauula

4.99 out of 5 average rating, 164 reviews

Moeʻuhane Kai Beach Front Home

Amazing beach front property on the East Shore of Oahu. 30-day minimum rental. Hear the waves from every room in the house. Very comfortable home, window units available, but you might rather open the five sets of French Doors & sliding glass door to enjoy the trade winds and ocean sounds. Great fishing right outside the back of the house. Ten minutes from the Polynesian Culture center and great food options. Great Thai food, malasadas, and Dole ice cream. Short drive to North Shore.

Guest favourite

Apartment in Kahuku

4.93 out of 5 average rating, 137 reviews

Tropical and Romantic Retreat with Inspired Design

Come enjoy this newly updated, designer inspired, spacious end-unit condo in beautiful Turtle Bay. It is as comfortable as it is beautiful. Whether it's breakfast in bed or a drink on the lanai swing, you may not want to leave this tropical paradise. Everything has been updated, including hand-picked pendants that can be dimmed to suit your mood. There is a nearby pool, beach and tropical walking trails. Restaurants and shops can be found at the newly renovated Turtle Bay hotel.

Guest favourite

Home in Haleiwa

4.96 out of 5 average rating, 177 reviews

Oceanfront Oahu North Shore Hawaii Private 3b Home

For rates less than 90 days. Please call or DM. Nestled on the shore of legendary Waimea Bay Point, this home is the gateway to an authentic Hawaiian experience. Lounge on the covered lanai feet from lapping surf watching whales, dolphins, turtles, surfers, and incredible sunsets. Extremely clean with all the necessities. Steps to 3 sandy beaches Waimea Bay, Shark’s Cove and Three Tables. This is the perfect family getaway, allowing you to live the true North Shore lifestyle.

Guest favourite

Apartment in Waikiki

4.92 out of 5 average rating, 148 reviews

Amazing Waikiki Beach Views!!

Perfect vacation getaway, with amazing views of Waikiki Beach and Lagoon!! Best location, walking distance to many points of interest, Ala Moana Mall/Designer stores and many restaurants! Enjoy visiting Oahu - there's sightseeing, swimming, hiking, surfing or shopping etc! Enjoy watching the fireworks every Friday nights from the patio, sponsored by Hilton Hawaiian Village! Hotel pool is also available for our guests. Also accepting long term stays at special rates.

Guest favourite

Cottage in North Shore

4.96 out of 5 average rating, 107 reviews

Tiny living! Quaint Haleiwa cottage

****Calendar is not always accurate, please inquire for availability. ******* Newly built cottage, equipped with everything to make your vacation a home away from home. High vaulted ceilings make the small home feel spacious, full kitchen for home cooked meals, a large covered deck for outdoor dining. In the heart of historic Haleiwa town, near Starbucks and 7-11, shopping and food trucks are down the street. We are located on site should you have any issues.

Guest favourite

Apartment in Kahuku

4.99 out of 5 average rating, 224 reviews

Modern & Contemporary North Shore Oahu Condo

Welcome to our beautiful condo tucked inside the dreamy North Shore of Oahu. Our place is located within the charming and gated community at Turtle Bay Resort called Kuilima Estates West. You will be within a 5-10 minute walk of breathtaking shorelines, world-class surfing, romantic dinners, and many adventures on both land and sea. Kuilima Estates is the only area of the north shore that allows legal vacation rentals.

Guest house in Kailua

4.78 out of 5 average rating, 143 reviews

Kailua Beach Cottage - 90/TVU-0287

WE HAVE PERMIT - 90/TVU-0287 FROM THE CITY & COUNTY WE WERE RATED BY AIRBNB AS A SUPERHOST. KAILUA BEACH RATED #1 BEACH IN AMERICA! This place is good for couples, business travelers, and families. (On the 2nd floor - upstairs) *Additional guest fee of $90 per person per day applies to parties over 4 people. Additional service fee and tax will apply. Visit the 8 Bdrm Villa website for a larger family group.

Guest house in Kailua

4.85 out of 5 average rating, 351 reviews

Kailua Palm Studio. Walk to Beach! PERMITTED

Licensed, legal 90/BB-0002 short term rental. *not impacted by Bill 41 (2022) **NEWLY RENOVATED BATHROOM AND KITCHENETTE (at end of June 2023)** Peaceful retreat in desirable Kailua! An easy 8-10 minute walk to Kailua Beach. Airbnb “Guest Favorite” awardee! Sister Unit: Kailua Pineapple Studio. Walk to Beach! PERMITTED. Property managed by Cynthia Rubinstein Real Estate, Inc. (License #RB-16858)

Holiday rentals for every style

Get the amount of space that is right for you

Villas

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Bungalows

Intimate homes, inviting architecture

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Convenient locations with everyday essentials

Popular amenities for Kailua holiday rentals

Free parking on premises

Air conditioning

Stay near Kailua's top sights

Kailua Beach Park200 locals recommend

Whole Foods Market370 locals recommend

Buzz's Steakhouse136 locals recommend

Pillbox Hike177 locals recommend

Boots & Kimo's Homestyle Kitchen51 locals recommend

Kailua Beach Adventures40 locals recommend

Other great holiday rentals in Kailua

Home in Kailua

4.88 out of 5 average rating, 17 reviews

Amazing Lanikai Beachfront Guest House!!

Guest favourite

Villa in Kailua

4.99 out of 5 average rating, 81 reviews

Honu Suite at La Bella’s-Walk to Beach-Licensed

Guest favourite

Guest house in Kailua

5 out of 5 average rating, 15 reviews

Private Bedroom with own bathroom & Garden

Guest favourite

Cottage in Kailua

4.92 out of 5 average rating, 37 reviews

Kailua Ohana Cottage close to beach

Home in Kailua

4.85 out of 5 average rating, 59 reviews

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Guest favourite

Rental unit in Kailua

5 out of 5 average rating, 38 reviews

Kailua Sunrise Studio ★ 1 Block to the Beach Park!

Guest favourite

Bungalow in Haleiwa

4.99 out of 5 average rating, 83 reviews

Bird Of Paradise TVU-1868 - Ke Iki Beach Bungalows

Guest favourite

Guest suite in Aina Haina

4.97 out of 5 average rating, 31 reviews

Sweeter than a suite

Quick stats about holiday rentals in Kailua

Total rentals
380 properties
Total number of reviews
11K reviews
Family-friendly rentals
200 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
100 properties have a pool
Rentals with dedicated workspaces
180 properties have a dedicated workspace

Destinations to explore